It’s Silhouette Challenge day!! This month’s challenge was to create a project for under $5 bucks. With Christmas right around the corner, I have a few holiday parties to go to this year. I thought what would be a fun and inexpensive gift was to make a few of these tumblers for some of my mom friends. My friend Michelle gave me the idea one day when she posted a cup that said “My Drinking Club has a Bunco Problem” AND she also tipped me off on these dollar store tumblers.  So I took to Pinterest to look for some other wine glass sayings.

These wine cups were really easy to make with the Silhouette machine. This project took me all of 10 minutes to actually do! So if you want to make a few of these tumblers to add to your gift stash this year  follow along.


You will need:

Design your saying in the Silhouette Studio or if you would like to use the designs I used you can download them here:



Once your vinyl has been cut, you will weed the design. Yes, I am using a dental pick. My mother in law is a retired dentist and gave me some of her old dental picks to use. The way I misplace craft tools I am so happy I have like 20 picks in a bucket. It works just as good as the hook tool. 😉


Once your design is ready to place on the cup it is time to transfer the design. I use contact paper to do that. I reuse this piece of contact paper for all three cups. I find that the less stickier it is the easier it is to work with.


Place you contact paper on the design and press/rub down. Peel off the contact paper and your design should now be on the contact paper. If it didn’t come down, just place it back on and press again.


Place your design on the cup and give it another rub. It might take a few times to get it released from the contact paper. Just press down, I use my nail to press down on the individual letters.


Then just peel off the contact paper. It should come off and your cup is done!


What was really fun about this project is that I got to play around with lettering. It was so neat to see something you hand lettered on paper end up on a glass! I love that my Silhouette machine can do that!

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I also played around with a few fonts and made a couple of other sayings.

Pair this funny tumbler with a bottle of wine and you have yourself a really cute and easy gift for your favorite wine drinker.



Want to Check Out More Silhouette Projects?

My Silhouette Challenge buddies and I are all sharing projects on our blogs today, so peruse the projects below for a wealth of Silhouette inspiration!

DIY Birthday Bib Simple and Stunning Winter Art Glittery Chipboard Gift Tags "Come Thou Fount" Stenciled Burlap Table Runner Happy & Vibrant Greeting Cards Bunco Water Bottle - White Elephant Gift Monogrammed Christmas Onesie Beautiful Thanksgiving Decor for Under $5 Wine Sippy Cups with Funny Sayings Thrifted Jewelry Box Makeover DIY Decorative Vinyl Christmas Gift Jar Harry Potter "Free Dobby" Odd Sock Collector Reindeer Candle Hurricanes with Washi Tape Plaid Star War Paper Play Ships Glitter & Paper Christmas Banner Upcycled Measuring Cup

1. From Wine to Whine // 2. Creative Ramblings // 3. Adventures in All Things Food // 4. unOriginal Mom // 5. Small Stuff Counts // 6. Alayna’s Creations // 7. Single Yet Married Mom // 8. Comfort and Yum // 9. Tori Grant Designs // 10. Cutesy Crafts // 11. The Crafting Nook // 12. Whatcha Workin’ On? // 13. Architecture of a Mom // 14. Havalah // 15. Create & Babble // 16. A Time For Seasons